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Unraveling the determinants of herbivorous insect diversity has been a significant challenge in ecology. Despite the strong association between insect and plant species, previous studies conducted in natural systems have shown great variation in the strength of the correlation between their species richness. Such variation could be attributed to the proportion of generalist insect species (generality). However, both higher and lower generality may weaken the correlation because (a) generalist insect species are less dependent on the number of plant species, and (b) specialist insect species utilize only a proportion of the total plant species. To explore these contradictory effects, we studied plant and herbivorous insect communities in seminatural grasslands in Japan. Plant–insect interactions were evaluated in a unique way with a particular focus on the staying and herbivory behaviors of insects, which reflect their habitat use as well as host use. We found that lower generality of insect communities strengthened the correlation between species richness of plants and insects, but this was not the case when plant species that had no interaction with insect species were also considered. This was because lower generality increased the number of plant species that did not interact with insects. The results indicate that insect generality has contradictory effects on the plant–insect diversity relationship, which emphasizes the importance of distinguishing the effects to understand the variation in the relationship between plant and insect diversity in natural systems. [ABSTRACT FROM AUTHOR]